What is a great personal question to ask a successful superior in a 1on1?

Not looking for the standard list of "good" questions to ask an interviewer that has been answered a couple dozen times here. I've recently come into a position with a successful superior at my firm that has allowed me occasional lunches to ask questions for my own development which he will answer candidly. We've worked together enough where I no longer need to attempt to impress him and all the standard face value questions have been asked.

So - what do you guys think are some great, more intimate personal/career questions to ask someone successful that can garner some pretty insightful responses? Thanks.

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